CN113896865A - 含多巴胺衍生侧链的萘酰亚胺聚合物半导体及其制备方法 - Google Patents
含多巴胺衍生侧链的萘酰亚胺聚合物半导体及其制备方法 Download PDFInfo
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Abstract
本发明涉及含多巴胺衍生侧链的萘酰亚胺聚合物半导体及其制备方法。本发明中的含多巴胺衍生侧链的萘酰亚胺聚合物具有在可见‑近红外区宽而强的吸收，可能归因于多巴胺衍生侧链含量的增加，提升了聚合物分子的固体堆积作用，探索新的衍生侧链，应用于新型萘酰亚胺构筑单元的设计，具有积极的研究意义。其侧链通过引入的多巴胺衍生结构单元对聚合物进行调控，且柔性侧链可为材料提供良好的溶解度，可溶解于氯仿、氯苯与甲苯等溶剂中，因此该材料可溶液加工。所以本发明作为半导体活性层给体材料在有机太阳能电池器件中有潜在的应用前景。
Description
技术领域
本发明涉及含多巴胺衍生侧链的萘酰亚胺聚合物半导体及其制备方法，属于有机太阳能电池材料领域。
背景技术
在光伏效应发现后的一百年内，太阳能电池得以问世，时至今日硅基太阳能电池已经凭借其超过20％的产业化的光电转化效率进入了许多领域之中，但是无机硅太阳能电池具有较高的生产成本以及在生产中无法避开的生态污染等缺点。有机太阳能电池相较下有许多优势，有机材料类型繁多，可以调控结构来优化其性质，比如吸光能力、电化学能级及载流子传输能力等，以此进一步优化光伏性能。有机半导体材料，特别是聚合物半导体材料，可以采用卷对卷(Roll to Roll)印刷大面积器件以及制作柔性器件。
萘二酰亚胺(NDI)是构建聚合物受体材料的重要结构单元。其中，研究最广、性能表现最好的聚合物N2200。N2200是高性能n-型聚合物半导体材料，它与一些高性能聚合物给体材料有较好的相容性、光学吸收互补性、电化学能级匹配性等特点。调控有机半导体材料光电性质的方法众多，其中之一就是通过分子的侧链工程对受体材料的光电性质进行调控。多巴胺作为人脑能够合成和释放上百种神经递质中最著名的小分子，其与多巴胺受体结合操控着脑区许多神经通道构成了大脑的奖励***。在聚合物体系中，多巴胺因为其独特的粘附性、亲水性、生物相容性以及水中良好的成膜性能得到应用。此外多巴胺的双酚基很容易引入助溶性的烷基链，形成杂化性的侧链单元，为聚合物材料提供良好的溶解性。
发明内容
本发明的目的是为了有机太阳能电池的光电转化效率，提供了含多巴胺衍生侧链的萘酰亚胺聚合物及其制备方法。所述的共轭聚合物具有制备工艺简单、光电性质优异、可溶液加工等优点，在有机太阳能电池受体材料领域有巨大的应用潜力。
本发明的目的是通过以下的技术方案实现的：
第一方面，本发明涉及含多巴胺衍生侧链的萘酰亚胺聚合物半导体及其制备方法，所述共轭聚合物的结构式如下所示：
第二方面，本发明涉及含多巴胺衍生侧链的萘酰亚胺聚合物半导体及其制备方法，包括如下步骤：
(1)按摩尔量份数，将单体M1，单体M2，甲基锡单体M3，催化剂和配体，溶于无水有机溶剂中；在氩气气氛下加热聚合后，经过索氏提取进行提纯，真空干燥获得深紫色的含多巴胺衍生侧链的萘酰亚胺聚合物。
优选地，步骤中，所述单体M1的结构式如下所示：
优选地，步骤中，所述单体M2的结构式如下所示：
优选地，步骤中，所述单体M3的结构式如下所示：
优选地，步骤中，所述单体M1，单体M2和单体M3的摩尔比为0.3：0.7：1。
优选地，步骤中，所述无水有机溶剂为无水甲苯、无水氯苯或四氢呋喃。
优选地，步骤中，所述催化剂为三(二亚苄基丙酮)二钯，配体为三(邻甲基苯基)磷。
优选地，步骤中，所述加热具体为：100℃下反应48小时；所述索氏提取依次采用的溶剂为甲醇、石油醚和氯仿。
(2)步骤(1)中所述的单体M1制备步骤如下:
a、按摩尔量份数，将1份3,4-二羟基苯乙基氨基甲酸叔丁酯与2.4份溴化烃以及2.1份碳酸钾加入到有机溶剂，以80℃反应12小时；反应结束后，经萃取干燥后得到中间化合物A，其结构式如下：
b、按摩尔量份数，将1份中间化合物A加到有机溶剂，室温下反应4小时；反应结束后，经硅胶柱提纯干燥后得到中间化合物B，其结构式如下：
c、按摩尔量份数，将1份2,6-二溴萘-1,4,5,8-四羧酸二酐(CAS:83204-68-6)与2.5份中间化合物B加到有机溶剂，以120℃反应12小时；反应结束后经硅胶柱提出干燥后得到单体M1。
优选地，步骤a中，所述的有机溶剂为N,N-二甲基甲酰胺，溴化烃为C1-C30溴化烷烃。
优选地，步骤b中，所述的有机溶剂为二氯甲烷与三氟乙酸混合溶剂。
优选地，步骤c中，所述的有机溶剂为乙酸。
本发明的显著优点为：
(1)本发明合成的含多巴胺衍生侧链的萘酰亚胺n-型聚合物，采用经典的Stille偶联缩聚，合成了一系列具有超高的数均分子量的聚合物。
(2)本发明所用到的原料均易获得且价格低，且合成工艺简单成熟，整体而言，合成成本低。
(3)本发明所制备的共轭聚合物，主链具有刚性平面的大π共轭结构，多巴胺侧链的引入形成杂化性的侧链单元，为聚合物材料提供良好的溶解性，使其具有作为有机场太阳能电池器件的潜力。
(4)本发明的聚合物具有较大的光吸收范围，良好的化学稳定性与热稳定性。
附图说明
图1为本发明实施例1中聚合物P的合成路线图。
图2为本发明实施例1中的单体M1核磁共振氢谱。
图3为本发明实施例1中的单体M1核磁共振碳谱。
图4为本发明实施例1中的聚合物P核磁共振氢谱。
图5为本发明实施例2中的聚合物P的薄膜紫外-可见光谱。
图6为本发明实施例2中的聚合物P的CV曲线。
图7为本发明实施例2中的聚合物P的热重曲线。
具体实施方式
下面结合具体实施例对本发明进行详细说明。以下实施例将有助于本领域的技术人员进一步理解本发明，但不以任何形式限制本发明。应当指出的是，对本领域的普通技术人员来说，在不脱离本发明构思的前提下，还可以做出若干变形和改进。这些都属于本发明的保护范围。
实施例1、含多巴胺衍生侧链的萘酰亚胺聚合物半导体的制备
本实施例提供1种含多巴胺衍生物侧链的萘酰亚胺聚合物，其结构式如下图所示，其合成路线参见图1。
1.1、单体M1的制备
单体M1的制备具体包括以下步骤：
(a)中间化合物A的合成
中间化合物A的结构式为
在氩气气氛下，将3,4-二羟基苯乙基氨基甲酸叔丁酯(14.84mmol)，葵基溴(35.62mmol)，碳酸钾(31.17mmol)和N,N-二甲基甲酰胺(20mL)加入双口瓶。将反应混合物在80℃下搅拌12小时后，待冷却至室温，用乙酸乙酯萃取，将所得有机相依次用水与饱和食盐水进行洗涤，再用无水硫酸镁干燥，过滤后通过减压除去溶剂。加入甲醇并冷冻(-18℃)，过滤收集产生的沉淀，真空干燥得到白色固体中间化合物A(产率为30％)。1H NMR(600MHz,CDCl3):δ6.81(d,J＝8.0Hz,1H),6.72–6.67(m,2H),4.52(s,1H),3.96(td,J＝6.7,4.2Hz,4H),3.34(d,J＝6.3Hz,2H),2.71(t,J＝6.8Hz,2H),1.84–1.75(m,4H),1.51–1.38(m,12H),1.40–1.09(m,28H),0.91–0.86(m,6H).
其中3,4-二羟基苯乙基氨基甲酸叔丁酯的合成参考文献：Maerten C,Garnier T,Lupattelli P,et al.Morphogen Electrochemically Triggered Self-Construction ofPolymeric Films Based on Mussel-Inspired Chemistry[J].Langmuir theAcs JournalofSurfaces&Colloids,2015:13385。
(b)中间化合物B的合成
中间化合物B的结构式为
在氩气气氛下，将中间化合物A(4.8mmol)和以体积比6：1比例配置的二氯甲烷与三氟乙酸混合物(7mL)加入双口瓶。将反应物在室温下反应4小时用20mL的5％浓度氢氧化钠水溶液淬灭反应后，用二氯甲烷萃取，所得有机相依次用水与饱和食盐水进行洗涤，然后用无水硫酸镁进行干燥，减压除去溶剂。通过快速硅胶柱纯化(洗脱剂为石油醚:乙酸乙酯＝7:1，体积比)，真空干燥后得到白色固体中间化合物B(产率为83％)。1H NMR(600MHz,CDCl3):δ6.81(d,J＝8.1Hz,1H),6.74–6.69(m,2H),3.97(dt,J＝8.8,6.7Hz,4H),2.94(t,J＝6.8Hz,2H),2.68(t,J＝6.8Hz,2H),1.82–1.77(m,4H),1.49–1.43(m,4H),1.34–1.21(m,24H),0.90–0.86(m,6H).
(c)单体M1的合成
单体M1的结构式为
在氩气气氛下，将2,6-二溴萘-1,4,5,8-四羧酸二酐(CAS:83204-68-6)(1.57mmol)、中间化合物B(3.94mmol)和无水乙酸(25ml)加入到双口瓶。在120℃下反应12小时，待反应物冷却至室温后，加入100ml冷水。过滤收集沉淀，并用甲醇洗涤得到粗产物。通过柱色谱法纯化(洗脱剂为二氯甲烷:石油醚＝5:1，体积比)，将产物溶于二氯甲烷，加入适量的石油醚，冷冻(-18℃)并过滤，得到白色固体单体M1(10.1％)。1H NMR(600MHz,CDCl3):δ9.00(s,2H),6.88(d,J＝2.0Hz,2H),6.85(dd,J＝8.1,2.0Hz,2H),6.81(d,J＝8.1Hz,2H),4.42–4.37(m,4H),3.98(dt,J＝18.9,6.7Hz,8H),2.98–2.94(m,4H),1.80(ddt,J＝14.7,12.6,6.3Hz,8H),1.49–1.43(m,8H),1.39–1.23(m,48H),0.91–0.85(m,12H).13CNMR(101MHz,Chloroform-d)δ160.67,147.98,139.07,130.63,121.22,114.72,114.16,69.45,69.34,42.94,33.58,31.95,29.70,29.67,29.64,29.62,29.50,29.48,29.41,29.39,26.10,26.07,22.72,14.16.
1.2、聚合物P的合成
聚合物P的结构式为
本发明对共轭聚合物的反应条件进行了多次优化，首先是对聚合所使用的溶剂进行优化，选择了邻二甲苯、2-甲基四氢呋喃等作为溶剂。此外，还对催化剂的量进行优化。最终优化结果如下：
在氩气氛围下，向耐压管中加入单体M1(0.06mmol)，单体M2(0.14mmol)，单体M3(0.2mmol)，和无水甲苯(0.4mL)，待搅拌溶解后加入三(二亚苄基丙酮)二钯(0.002mmol)和三(邻甲基苯基)膦(0.008mmol)，液上除氧10min，封管。在100℃下反应48小时，待反应物冷却至室温，加入甲醇后减压过滤得粗产物。将粗产物依次用甲醇，石油醚和氯仿进行索氏提取，收集氯仿提取片段，减压去除溶剂，加入甲醇得到沉淀，过滤后真空干燥得到目标聚合物P(99.8％)。1H NMR(400MHz,Chloroform-d)δ8.83(s,1H),8.51(s,1H),7.34(s,4H),6.82(s,1.8H),4.38(s,1.2H),4.13(s,2.8H),3.96(s,2.4H),2.95(s,1.2H),1.25(s,64H),0.85(s,12H).Mn＝127.6kDa，Mw＝345.6kDa，PDI＝2.70。
其中，单体M2购买自阿拉丁(CAS:1100243-35-3)；单体M3购买自阿拉丁(CAS:86134-26-1)。
实施例2、聚合物P的紫外吸收光谱、电化学性质和热稳定性
2.1、聚合物P的紫外吸收光谱
图5给出了聚合物P在氯苯溶液和薄膜时的的紫外吸收光谱。对比薄膜吸收和溶液吸收性质可知，两者的吸收峰没有出现明显的宽化特点，这与材料良好的分子堆叠有关。在450～850nm长波长吸收范围，聚合物薄膜吸收，相比于溶液吸收，具有更强的吸收特性。表明各聚合物薄膜内分子的堆积作用更强，分子内的电荷转移作用更明显。聚合物P在可见光区的吸收强度大，吸收峰宽，这可能与其引入了最多的多巴胺衍生侧链相关。聚合物P薄膜的起始吸收波长(λonsetfilm)在863nm左右，由此可计算出Egfilm＝1.44eV(Egfilm＝1240/λonsetfilm eV)，说明该聚合物是一个窄带隙聚合物。
2.2、聚合物P的电化学性质
以铂片为工作电极，铂丝为对电极，Ag/AgNO3电极为参比电极，0.1M的四丁基六氟磷酸铵乙腈溶液为电解质，二茂铁为标定物，扫描速度为60mV/s，在铂片上对聚合物进行了测试。图6给出了测试所得到的聚合物的电化学曲线。根据公式可计算其能级与能隙：ELUMO＝﹣(Ere onset+4.33)eV，Eg＝ELUMO－EHOMO，其中Ere onset是起始还原电势。
由图6可知，聚合物P的Ere onset为-0.54eV。根据给出的公式可计算出，聚合物P的LUMO能级为-3.79eV。从其能级的角度看其可以作为受体材料。
2.3、聚合物P的热稳定性
图7给出聚合物P的热分解温度在400℃以上，说明聚合物P具有良好的热稳定性。
2.4、聚合物P的溶解性
聚合物P室温下在氯仿、氯苯等溶剂中具有较好的溶解性，为其可溶液处理提供了保证。
以上所述仅为本发明的较佳实施例，凡依本发明申请专利范围所做的均等变化与修饰，皆应属本发明的涵盖范围。
Claims (10)
1.含多巴胺衍生侧链的萘酰亚胺聚合物，其特征在于，所述聚合物的结构式如下所示：
2.如权利要求1所述的含多巴胺衍生侧链的萘酰亚胺聚合物的制备方法，其特征在于，包括如下步骤：
将单体M1，单体M2，甲基锡单体M3，催化剂和配体，溶于无水有机溶剂中；在氩气气氛下加热聚合后，经过索氏提取进行提纯，真空干燥获得深紫色的含多巴胺衍生侧链的萘酰亚胺聚合物。
3.根据权利要求2所述的含多巴胺衍生侧链的萘酰亚胺聚合物的制备方法，其特征在于，所述单体M1的结构式如下所示：
4.根据权利要求3所述的含多巴胺衍生侧链的萘酰亚胺聚合物的制备方法，其特征在于，所述单体M1具体制备步骤为：
a、按摩尔量份数，将1份3,4-二羟基苯乙基氨基甲酸叔丁酯与2.4份溴化烃以及2.1份碳酸钾加入到有机溶剂，以80℃反应12小时；反应结束后，经萃取干燥后得到中间化合物A，其结构式如下：
b、按摩尔量份数，将1份中间化合物A加到有机溶剂，室温下反应4小时；反应结束后，经硅胶柱提纯干燥后得到中间化合物B，其结构式如下：
c、按摩尔量份数，将1份2,6-二溴萘-1,4,5,8-四羧酸二酐与2.5份中间化合物B加到有机溶剂，以120℃反应12小时；反应结束后经硅胶柱提出干燥后得到单体M1。
5.根据权利要求4所述的含多巴胺衍生侧链的萘酰亚胺聚合物的制备方法，其特征在于，所述步骤a有机溶剂为N,N-二甲基甲酰胺，溴化烃为C1-C30溴化烷烃；所述步骤b有机溶剂为二氯甲烷与三氟乙酸混合溶剂；所述步骤c有机溶剂为乙酸。
6.根据权利要求2所述的含多巴胺衍生侧链的萘酰亚胺聚合物的制备方法，其特征在于，所述单体M2的结构式如下所示：
7.根据权利要求2所述的含多巴胺衍生侧链的萘酰亚胺聚合物的制备方法，其特征在于，所述单体M3的结构式如下所示：
8.根据权利要求2所述的含多巴胺衍生侧链的萘酰亚胺聚合物的制备方法，其特征在于，所述催化剂为三(二亚苄基丙酮)二钯，配体为三(邻甲基苯基)磷；所述无水有机溶剂为无水甲苯、无水氯苯或四氢呋喃；所述单体M1，单体M2和单体M3的摩尔比为0.3：0.7：1。
9.根据权利要求2所述的含多巴胺衍生侧链的萘酰亚胺聚合物的制备方法，其特征在于，所述加热具体为：100℃下反应48小时；所述索氏提取依次采用的溶剂为甲醇、石油醚和氯仿。
10.根据权利要求1所述的含多巴胺衍生侧链的萘酰亚胺聚合物半导体的应用，其特征在于，所述含多巴胺衍生侧链的萘酰亚胺聚合物作为半导体活性层给体材料在有机太阳能电池器件中的应用。
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